Amphiphilic macrocycles bearing biofragment: Molecular design as factor controlling self-assembly

Materials Science and Engineering C

Volumn 38, Issue 1, 2014, Pages 143-150

  Zakharova, L Ya ^a   Semenov, V E ^a   Syakaev, V V ^a   Voronin, M A ^a   Gabdrakhmanov, D R ^a   Valeeva, F G ^a   Mikhailov, A S ^a   Voloshina, A D ^a   Reznik, V S ^a   Latypov, Sh K ^a   Konovalov, A I ^a  

^a A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

Amphiphile; Geometry and energetic factors; Self assembly; Uracilophane

Indexed keywords

4-NITROPHENOL; MACROCYCLIC COMPOUND; NITROPHENOL; SOLUTION AND SOLUBILITY; SURFACTANT; URACIL;

CHEMISTRY; CONDUCTOMETRY; DIFFUSION; ELECTRIC CONDUCTIVITY; HYDROLYSIS; LIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARTICLE SIZE; RADIATION SCATTERING; SOLUTION AND SOLUBILITY; SPECTROFLUOROMETRY; SURFACE TENSION; SYNTHESIS; TEMPERATURE;

CONDUCTOMETRY; DIFFUSION; ELECTRIC CONDUCTIVITY; HYDROLYSIS; LIGHT; MACROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; NITROPHENOLS; PARTICLE SIZE; SCATTERING, RADIATION; SOLUTIONS; SPECTROMETRY, FLUORESCENCE; SURFACE TENSION; SURFACE-ACTIVE AGENTS; TEMPERATURE; URACIL;

EID: 84894476940     PISSN: 09284931     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.msec.2014.01.057     Document Type: Article

References (54)

1. J.H. Fendler Membrane Mimetic Chemistry: Characterizations and Applications of Micelles, Microemulsions, Monolayers, Bilayers, Vesicles, Host-Guest Systems, and Polyions 1982 Wiley New York
2. J.H. Fendler Atomic and molecular clusters in membrane mimetic chemistry Chem. Rev. 87 1987 877 899
3. J.A. Zasadzinski, E. Kisak, and C. Evans Complex vesicle-based structures Curr. Opin. Colloid Interface Sci. 6 2001 85 90 (Pubitemid 32233071)
4. F. Cuomo, M. Mosca, S. Murgia, P. Avino, A. Ceglie, and F. Lopez Evidence for the role of hydrophobic forces on the interactions of nucleotide- monophosphates with cationic liposomes J. Colloid Interface Sci. 410 2013 140 145
5. C.A. Hunter Sequence-dependent DNA structure: the role of base stacking interactions J. Mol. Biol. 230 1993 1025 1054 (Pubitemid 23159942)
6. D. Vollhardt Effect of interfacial molecular recognition of non-surface-active species on the main characteristics of monolayers Adv. Colloid Interface Sci. 116 2005 63 80 (Pubitemid 41654902)
7. B. Liu, H.-L. Zhang, J. Liu, Yu.-D. Zhao, Q.-M. Luo, and Zh.-L. Huang Novel pyrimidine-based amphiphilic molecules: synthesis, spectroscopic properties and applications in two-photon fluorescence microscopic imaging J. Mater. Chem. 17 2007 2921 2929 (Pubitemid 47152327)
8. M. Thies, M. Poschmann, U. Hinze, and H.H. Paradies Light scattering on micellar solutions of N, N′-butyl-n-alkyl-1,4-diazabicyclo-[2,2,2]-octane derivatives of 3′-O-acylthymidine-5′-phosphates Colloids Surf A 101 1995 159 177
9. L. Zakharova, M. Voronin, D. Gabdrakhmanov, V. Semenov, R. Giniyatullin, V. Syakaev, Sh. Latypov, V. Reznik, A. Konovalov, and Yu. Zuev Supramolecular systems based on novel mono- and dicationic pyrimidinic amphiphiles and oligonucleotides: a self-organization and complexation study ChemPhysChem 13 2012 788 796
10. M.A. Voronin, D.R. Gabdrakhmanov, R.N. Khaibullin, I.Yu. Strobykina, V.E. Kataev, B.Z. Idiyatullin, D.A. Faizullin, Yu.F. Zuev, L.Ya. Zakharova, and A.I. Konovalov Novel biomimetic systems based on amphiphilic compounds with a diterpenoid fragment: role of counterions in self-assembly J. Colloid Interface Sci. 405 2013 125 133
11. D.R. Gabdrakhmanov, M.A. Voronin, L.Ya. Zakharova, A.I. Konovalov, R.N. Khaybullin, I.Yu. Strobykina, V.E. Kataev, D.A. Faizullin, N.E. Gogoleva, T.A. Konnova, V.V. Salnikov, and Yu.F. Zuev Supramolecular design of biocompatible nanocontainers based on amphiphilic derivatives of a natural compound isosteviol Phys. Chem. Chem. Phys. 15 2013 16725 16735
12. D. Attwood The mode of association of amphiphilic drugs in aqueous solution Adv. Colloid Interface Sci. 55 1995 271 303
13. N. Basilio, V. Francisco, and L. Garcia-Rio Aggregation of p-sulfonatocalixarene-based amphiphiles and supra-amphiphiles Int. J. Mol. Sci. 14 2013 3140 3157
14. D.L. Akins, H.-R. Zhu, and Ch. Guo Aggregation of tetraaryl-substituted porphyrins in homogeneous solution J. Phys. Chem. 100 1996 5420 5425 (Pubitemid 126790510)
15. V.V. Syakaev, E.Kh. Kazakova, Ju.E. Morozova, Ya.V. Shalaeva, Sh.K. Latypov, and A.I. Konovalov Guest controlled aggregation of amphiphilic sulfonatomethylated calix[4]resorcinarenes in aqueous solutions J. Colloid Interface Sci. 370 2012 19 26
16. J. Li, W. Zhou, J. Yang, X. Lang, and P. Huang One-dimensional self-assembly of phenylacetylene macrocycles: effect of peripheral substituents J. Colloid Interface Sci. 395 2013 99 103
17. L.Ya. Zakharova, V.E. Semenov, M.A. Voronin, F.G. Valeeva, A.R. Ibragimova, R.Kh. Giniatullin, A.V. Chernova, S.V. Kharlamov, L.A. Kudryavtseva, Sh.K. Latypov, V.S. Reznik, and A.I. Konovalov Nanoreactors based on amphiphilic uracilophanes: self-organization and reactivity study J. Phys. Chem. B 111 2007 14152 14162 (Pubitemid 351147674)
18. D. Pasini, and M. Ricci Macrocycles as precursors for organic nanotubes Curr. Org. Synth. 4 2007 59 80
19. G.W. Gokel, and S. Negin Synthetic Ion channels: from pores to biological applications Acc. Chem. Res. 46 12 2013 2824 2833
20. S. Höger, D.L. Morrison, and V. Enkelmann Solvent triggering between conformational states in amphiphilic shape-persistent macrocycles J. Am. Chem. Soc. 124 2002 6734 6736 (Pubitemid 34602665)
21. D.W. Fitzpatrick, and H.J. Ulrich Macrocyclic Chemistry: New Research Developments 2010 Nova Science Publishers Inc. New York
22. A.J. Helsel, A.L. Brown, K. Yamato, W. Feng, L. Yuan, A.J. Clements, S.V. Harding, G. Szabo, Zh. Shao, and B. Gong Highly conducting transmembrane pores formed by aromatic oligoamide macrocycles J. Am. Chem. Soc. 130 2008 15784 15785
23. T.J. Hubin Synthesis and coordination chemistry of topologically constrained azamacrocycles Coord. Chem. Rev. 241 2003 27 46
24. X. Li, and Y. Zhao Oligocholate foldamer with 'prefolded' macrocycles for enhanced folding in solution and surfactant micelles Tetrahedron 69 2013 6051 6059
25. V.E. Semenov, R.Kh. Giniatullin, A.S. Mikhailov, A.E. Nikolaev, S.V. Kharlamov, Sh.K. Latypov, and V.S. Reznik Unusual reaction of macrocyclic uracils with paraformaldehyde Eur. J. Org. Chem. 28 2011 5423 5426
26. S. Sameni, C. Jeunesse, D. Matt, and J. Harrowfield Calix[4]arene daisychains Chem. Soc. Rev. 38 2009 2117 2146
27. P. Stilbs Fourier transform pulsed-gradient spin-echo studies of molecular diffusion Prog. Nucl. Magn. Reson. Spectrosc. 19 1987 1 45
28. O. Soderman, and P. Stilbs NMR studies of complex surfactant systems Prog. Nucl. Magn. Reson. Spectrosc. 26 1994 445 482 (Pubitemid 124003832)
29. Y. Cohen, L. Avram, and L. Frish Diffusion NMR spectroscopy in supramolecular and combinatorial chemistry: an old parameter - new insights Angew. Chem. Int. Ed. 44 2005 520 554 (Pubitemid 40192558)
30. D. Wu, A. Chen, and C.S. Johnson An improved diffusion-ordered spectroscopy experiment incorporating bipolar-gradient pulses J. Magn. Reson. Ser. A 115 1995 260 264
31. T. Masanori Application of a generating function to reaction kinetics in micelles. Kinetics of quenching of luminescent probes in micelles Chem. Phys. Lett. 33 2 1975 289 292
32. N.J. Turro, and A. Yekta Luminescent probes for detergent solutions. A simple procedure for determination of the mean aggregation number of micelles J. Am. Chem. Soc. 100 1978 5951 5952
33. K. Kalyanasundaran, and J.K. Thomas Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems J. Am. Chem. Soc. 99 1977 2039 2044
34. K. Holmberg, B. Jönsson, B. Kronberg, and B. Lindman Surfactants and Polymers in Aqueous Solution 2002 John Wiley & Sons Ltd. Chichester
35. G.A. Gainanova, G.I. Vagapova, A.R. Ibragimova, F.G. Valeeva, V.V. Syakaev, E.V. Tudriy, I.V. Galkina, O.N. Kataeva, L.Ya. Zakharova, Sh.K. Latypov, and A.I. Konovalov Self-assembling systems based on amphiphilic alkyltriphenylphosphonium bromides: elucidation of the role of head group J. Colloid Interface Sci. 367 2012 327 336
36. L.Ya. Zakharova, V.V. Syakaev, M.A. Voronin, V.E. Semenov, F.G. Valeeva, A.R. Ibragimova, A.V. Bilalov, R.Kh. Giniyatullin, Sh.K. Latypov, V.S. Reznik, and A.I. Konovalov New self-assembling systems based on bola-type pyrimidinic surfactants J. Colloid Interface Sci. 342 2010 119 127
37. P. Stilbs, and B. Lindmann Determination of organic counterion binding to micelles through Fourier transform NMR self-diffusion measurements J. Phys. Chem. 85 1981 2587 2589
38. M. Jansson, and P. Stilbs A comparative study of organic counterion binding to micelles with the Fourier transform NMR self-diffusion technique J. Phys. Chem. 89 1985 4868 4873
39. 16TPB) in aqueous medium: their interfacial, bulk and fluorescence quenching behaviour J. Chem. Sci. 122 2 2010 109 117
40. L. Zhou, X. Jiang, Y. Li, Z. Chen, and X. Hu Synthesis and properties of a novel class of Gemini pyridinium surfactants Langmuir 23 2007 11404 11408 (Pubitemid 350132976)
41. D.T. Cramb, and S.C. Beck Fluorescence quenching mechanisms in micelles: the effect of high quencher concentration J. Photochem. Photobiol. A 134 2000 87 95
42. J.N. Israelachvili, D.J. Mitchell, and B.W. Ninhem Theory of self-assembly of hydrocarbon amphiphiles into micelles and bilayers J. Chem. Soc. Faraday Trans. 2 72 1976 1525 1568
43. V. Arora, H.M. Chawla, and S.P. Singh Calixarenes as sensor materials for recognition and separation of metal ions ARKIVOC ii 2007 172 200
44. T. Ogoshi, and A. Harada Chemical sensors based on cyclodextrin derivatives Sensors 8 2008 4961 4982
45. L.Ya. Zakharova, and A.I. Konovalov Supramolecular systems based on cationic surfactants and amphiphilic macrocycles Colloid J. 74 2 2012 194 206
46. L. Basabe-Desmonts, D.N. Reinhoudt, and M. Crego-Calama Design of fluorescent materials for chemical sensing Chem. Soc. Rev. 36 2007 993 1017
47. G. Ziyatdinova, E. Ziganshina, and H. Budnikov Surfactant media for constant-current coulometry. Application for the determination of antioxidants in pharmaceuticals Anal. Chim. Acta. 744 2012 23 28
48. G.A. Evtugyn, E.E. Stoikova, and R.V. Shamagsumova Molecular receptors and electrochemical sensors based on functionalized calixarenes Russ. Chem. Rev. 79 12 2010 1071 1097
49. N.A. Vodolazkaya, Y.A. Gurina, N.V. Salamanova, and N.O. Mchedlov-Petrossyan Spectroscopic study of acid-base ionization and tautomerism of fluorescein dyes in direct microemulsions at high bulk ionic strength J. Mol. Liq. 145 2009 188 196
50. N.O. Mchedlov-Petrossyan, L.N. Vilkova, N.A. Vodolazkaya, A.G. Yakubovskaya, R.V. Rodik, V.I. Boyko, and V.I. Kalchenko The nature of aqueous solutions of a cationic calix[4]arene: a comparative study of dye-calixarene and dye-surfactant interactions Sensors 6 8 2006 962 977
51. Yu.V. Isaenko, N.A. Vodolazkaya, and N.O. Mchedlov-Petrossyan Reporter molecules for nanosized lyophilic dispersions. 2,6-dichloro-4-(2,4,6- triphenylpyridinium-1-yl)phenolate in aqueous micellar solutions of colloidal surfactants Funct. Mater. 13 3 2006 423 425
52. N.O. Mchedlov-Petrossyan, N.A. Vodolazkaya, O.N. Bezkrovnaya, A.G. Yakubovskaya, A.V. Tolmachev, and A.V. Grigorovich Fluorescent dye N, N′-dioctadecylrhodamine as a new interfacial acid-base indicator Spectrochim. Acta, Part A 69 2008 1125 1129 (Pubitemid 351380502)
53. E.P. Zhiltsova, V.V. Syakaev, S.S. Lukashenko, A.P. Timosheva, R.R. Kashapov, Sh.K. Latypov, L.Ya. Zakharova, and A.I. Konovalov Diffusivity data and reaction kinetics as probes for self-assembling: cationic surfactant-chloroform system Fluid Phase Equilib. 360 2013 16 22
54. L.Ya. Zakharova, E.P. Zhiltsova, A.B. Mirgorodskaya, L.A. Kudryavtseva, and A.I. Konovalov Catalysis of nucleophilic substitution reactions in supramolecular systems Russ. Chem. Bull. 53 7 2004 1385 1401 (Pubitemid 39434574)